Synthesis and biological evaluation of 1-(5-(2-chloroquinolin-3-yl)-3-phenyl-1H-pyrazol-1-yl)ethanone derivatives as potential antimicrobial agents

Miniyar, Pankaj B.; Barmade, Mahesh A.; Mahajan, Anand A.

doi:10.1016/j.jscs.2013.12.004

Cited by 21 publications

(12 citation statements)

References 18 publications

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“…Step: 1 Synthesis of Quinolines: [11][12][13][14][15][16] Take accurately weighed amount of substituted aniline (0.1 Mol) into a round-bottomed flask and add 0.1 mol of dimethylformamide (7.7 ml) and phosphorous oxytrichloride 0.01 mol (0.2 ml).…”

Section: Experimental: Methodologymentioning

confidence: 99%

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2020

IJPSR

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Quinolines bears a very good synthon so that a variety of novel heterocyclic with good pharmaceutical profile can be designed. There are various biological activities for quinolones such as antibacterial, antimalarial and various drugs possessing quinolone as nucleus are ciprofloxacin (Cipro), lomefloxacin (Maxaquin), norfloxacin (Noroxin), ofloxacin (Floxin), moxifloxacin (Avelox) and levofloxacin (Levaquin). So, in the present work 2chloro quinoline 3-carbaldehyde containing quinolines were synthesized by using solvent conservation techniques like reflux technique. Various quinolines derivatives were synthesized by the condensation reaction between dimethylformamide, PoCl 3, and different substituted aniline to give 2-chloro 3carbaldehyde (1a). The reaction of 2-chloro 3-carbaldehyde with metformin gives quinolines Schiff bases as final compound (2a-2d). The obtained product was purified and structures were confirmed by TLC, MP & IR spectroscopy. All the compounds were screened for in-vitro anti-inflammatory activity using diclofenac sodium as standard by using protein denaturation method. Further, the selected compounds also studied for anti-inflammatory activity by in-vitro methods and anti-oxidant activity by hydrogen peroxide methods. Some of the compounds have shown significant activities compared to standard.

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Section: Experimental: Methodologymentioning

confidence: 99%

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2020

IJPSR

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“…Compound 29 (Fig. 16) (p-amino derivative) was found to be more promising antifungal agent with MIC = 46 µg/ml against P. notatum and MIC = 48 µg/ml against A. fumigatus relative to reference drug with MIC = 30.5 & 32.5 µg/ml, respectively [46].…”

Section: Antifungal Activitymentioning

confidence: 99%

“…In search of efficient antimicrobial agents, chloroquinolinepyrazole derivatives were synthesized by Miniyar et al in 2015. Compound 16 ( Figure 9) was found to be good inhibitor against gram +ve B. subtilis and gram -ve E. coli with MIC = 54 µg/ml and 43 µg/ml relative to reference drug Gatifloxacin with 30 µg/ml and 28.5 µg/ml, respectively [46]. In order to develop novel potential antibacterial agents, Li et al in 2015 reported the synthesis of hybrid pyrazole derivative 19 with aminoguanidine moiety.…”

Section: Antibacterial Activitymentioning

confidence: 99%

Pyrazole Bearing Molecules as Bioactive Scaffolds: A Review

Aziz

Zahoor

Ahmad

2020

J. Chil. Chem. Soc.

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Pyrazole being a heterocyclic motif has secured an eccentric status in the field of medicinal chemistry. Pyrazole and its derivatives have tremendous biological applications like anti-cancer, anti-microbial, antiviral, antifungal, anti-inflammatory, analgesic, insecticidal etc. In this review, some recent developments have been reported for the synthesis of biologically active pyrazole based molecules having biological potential such as anti-SIRT1 and SIRT2, anti-FAAH, anti-NOSs, as liver X receptor partial agonist, CB2 receptor ligand and glucagon receptor antagonists.

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“…The bound quinoline‐pyrazole, pyrazole‐triazole and quinoline‐triazole scaffolds containing heterocyclic compounds have received attention due to their potential antimicrobial activity (Figure ). Quinoline clubbed with pyrazole has been reported for antibacterial, antifungal, antitubercular, anticancer, activities. Pyrazolyl‐triazole were reported for antibacterial, antifungal, and anticancer activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of New 1,2,3‐Triazolyl‐Pyrazolyl‐Quinoline Derivatives as Potential Antimicrobial Agents

et al. 2020

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A new series of 4-{1-phenyl-4-[(4-phenyl-1,2,3-triazol-1-yl)methyl]pyrazol-3-yl}quinoline (7a-l) have been synthesized by a click reaction of 4-(4-(azidomethyl)-1-phenyl-1H-pyrazol-3-yl) quinoline (5a-d) with a substituted ethynylbenzene. The newly synthesized 1,2,3-triazolyl-pyrazolyl-quinoline derivatives were evaluated for biological activity against Escherichia coli (NCIM 2574), Proteus mirabilis (NCIM 2388), (Gram negative strains), Bacillus subtilis (NCIM 2063), Staphylococcus albus (NCIM 2178) (Gram positive strains) and in vitro antifungal activity against Candida albicans (NCIM 3100) and Aspergillus niger (ATCC 504). Five 1,2,3-triazolyl-pyrazolyl-quinoline derivatives, 7d, 7 g, 7 h, 7k and 7 l exhibited good antifungal activity against A. niger with MIC 62.5 μg/mL. The compounds 7 h, 7k and 7 l were further evaluated for ergosterol inhibition assay against A. niger cell sample at 62.5 μg/mL concentration. Upon analysis of the sterol inhibition assay, it was revealed that, the ergosterol biosynthesis has decreased in the fungal samples treated with the 1,2,3-triazolyl-pyrazolyl-quinoline derivatives. Thus antimicrobial activity suggested that, these compounds could aid and assist in the development of lead compounds to treat microbial infections.

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Synthesis and biological evaluation of 1-(5-(2-chloroquinolin-3-yl)-3-phenyl-1H-pyrazol-1-yl)ethanone derivatives as potential antimicrobial agents

Cited by 21 publications

References 18 publications

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Pyrazole Bearing Molecules as Bioactive Scaffolds: A Review

Synthesis and Biological Evaluation of New 1,2,3‐Triazolyl‐Pyrazolyl‐Quinoline Derivatives as Potential Antimicrobial Agents

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